New access to methyl formylcyclopropanecarboxylates via diethylaminotrimethylsilane mediated tandem nucleophilic reaction of aldehyde with methyl 2,3-dihalopropanoate

被引:12
作者
Hagiwara, H
Komatsubara, N
Hoshi, T
Suzuki, T
Ando, M
机构
[1] Niigata Univ, Grad Sch Sci & Technol, Niigata 9502181, Japan
[2] Niigata Univ, Fac Engn, Niigata 9502181, Japan
关键词
aldehydes; cyclopropanation; halo esters; Michael reactions;
D O I
10.1016/S0040-4039(98)02668-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Formylcyclopropanecarboxylates have been synthesized by diethylaminotrimethylsilane mediated tandem conjugate addition-alkylation of aldehydes to methyl alpha-haloaclylate generated in situ from methyl 2,3-dihalopropanoate. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1523 / 1526
页数:4
相关论文
共 9 条
[1]   1,5-DICARBONYL COMPOUNDS - A GENERAL PREPARATION METHOD [J].
DUHAMEL, P ;
HENNEQUIN, L ;
POIRIER, JM ;
TAVEL, G ;
VOTTERO, C .
TETRAHEDRON, 1986, 42 (17) :4777-4786
[2]  
ELIEL E, 1963, J AM CHEM SOC, V79, P5986
[3]  
FRANKE W, 1953, CHEM ABST 2205A, V37
[4]   Tandem nucleophilic reaction of 1,3-dicarbonyl compounds to methyl alpha-bromoacrylate: [3+2]heteroannulation leading to hydrofuran derivatives [J].
Hagiwara, H ;
Sato, K ;
Suzuki, T ;
Ando, M .
TETRAHEDRON LETTERS, 1997, 38 (12) :2103-2106
[5]   Double Michael addition reaction of oxophorone and its derivatives leading to bicyclo[2.2.2]octane compounds [J].
Hagiwara, H ;
Yamada, Y ;
Sakai, H ;
Suzuki, T ;
Ando, M .
TETRAHEDRON, 1998, 54 (37) :10999-11010
[6]   Direct 1,4-addition of aldehydes to vinylketones [J].
Hagiwara, H ;
Kato, M .
TETRAHEDRON LETTERS, 1996, 37 (29) :5139-5140
[7]   BICYCLOANNULATION OF ALPHA-BROMO ALPHA,BETA-UNSATURATED ESTERS - SYNTHESIS OF THE TRICYCLO[4.4.0.0(1,5)]DECANE FRAMEWORK AND ITS CONGENERS [J].
HAGIWARA, H ;
ABE, F ;
UDA, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (21) :2651-2655
[8]   STEREOSELECTIVE SYNTHESIS OF (-)-ACORENONE AND (-)-ACORENONE-B - ABSOLUTE-CONFIGURATION OF NATURAL (-)-ACORENONE [J].
PESARO, M ;
BACHMANN, JP .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (05) :203-204
[9]   ENAMINE ALKYLATION AND ACYLATION OF CARBONYL COMPOUNDS [J].
STORK, G ;
SZMUSZKOVICZ, J ;
TERRELL, R ;
BRIZZOLARA, A ;
LANDESMAN, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (02) :207-&